The Inmate-Turned-CEO Changing Lives While Keeping America Moving

Jason Wang was not living the American Dream. Born to immigrant parents who came to the U.S. without friends or relatives, barely speaking English and working low wage jobs, the family was extremely poor and lived in neighborhoods where police sirens and gunshots were background noise. Racial slurs greeted him at school.

The target of his father’s violent temper, Wang’s childhood memories include being chased around the kitchen with a butcher knife and told he would never amount to anything. At 8 years old, his father stripped him naked, stomped and kicked him, and threw him outside in a negative ten-degree Iowa blizzard to fend for himself.

At 13, without a supportive home environment and no one to turn to at school, a gang leader became his father figure, a street gang the family he didn’t have. They loved him, respected him, and taught him what they knew: robbery. Arrested at 15 for first degree felony aggravated robbery and sentenced to a maximum-security prison for 12 years, Wang was destined for a prison cell, not the boardroom.

Yet that’s where he is now. As founding CEO of FreeWorld, Wang and his team “get formerly incarcerated people into high-wage jobs to thrive on their own terms.” They do this by training them to get their commercial drivers license and placing them in the high-pay, low-supply trucking industry. But more than that, they remove the barriers to earning that license and job, increase graduates’ self-worth, and keep them out of jail as productive members of society responsible for keeping the nation’s economy moving. Wang shared his inspiring story of reinvention, and of life in the “free world,” prison slang for life on the outside.

How did you reinvent yourself from inmate to cum laude graduate of the University of Texas with two graduate degrees, to founder of FreeWorld?

Jason Wang: My mom used to drive 14 hours every single weekend just to see me for two hours in prison. And this was after working a 12-hour night shift. And it’s because of her dedication and love for me that I decided to turn my life around. She sent me huge packages of books and math homework and would test me during visitation. She instilled in me that education could be the key that unlocks the future I didn’t even know could happen.

In 2007, the media found out that corrections officers were sexually assaulting teenage boys and girls, human rights and physical abuses that I witnessed firsthand. By then I was a trusted inmate because I had set up General Educational Development (GED) and Bible study programs. So as a well-behaved inmate, I was selected to testify at a Texas Senate hearing. The old adage is that kids are the future, but you have kids languishing inside prisons with no educational or training opportunities. What most of us saw was somebody getting released only to come right back to prison or get killed on the streets. So naturally we didn’t care about our future because we all figured we’d be dead by 21.

I didn’t know this at the time, but I became a big name in the juvenile justice reform movement in Texas. This allowed me to work with the independent ombudsman to enact sweeping changes, and our work resulted in releasing 5,000 kids to community programs where they could be better served. And because of the work we did, I was released after serving three and a half years and received a full scholarship to the University of Texas at Dallas.

What is your startup story?

Wang: About two years before we founded FreeWorld in 2018, I met venture capitalist and CEO coach Matt Mochary and venture capitalist Jason Green at a prison event hosted by Defy Ventures, a nonprofit organization that essentially creates a Shark Tank-like event for prisons. Matt had helped 10 to 20 former inmates get a commercial driver’s license in the trucking industry. Green encouraged him to scale it across the country, but Matt wanted someone with a criminal history to lead the organization. And so my life changed because of Matt and Jason. They selected me as the founding CEO and gave me the resources to test and scale it to multiple cities and continue to provide guidance and coaching to build the team and scale our impact nationwide.

Along with technologist and entrepreneurentrepreneur Andy Bromberg, these three board members shaped my thinking on how to build the company. I previously had the old nonprofit, brick and mortar model in mind: hyper local, serving a hundred people a year. They pushed me to figure out a way to not only create a tech platform that can scale across the United States and potentially help millions of people, but also put together the beginnings of a business model that would allow our nonprofit to be self-sustaining. Because to be able to serve this huge population, we need massive amounts of capital and it’s very challenging to raise capital in the nonprofit world.

Why trucking? What other industries did you consider?

Wang: The thesis of the organization is that poverty leads to incarceration. Most people who go to prison are poor. And if you can afford a good attorney, oftentimes you get away with things other people wouldn’t. The idea is that when somebody gets released from the prison system, they can’t find a job with their criminal record. They can’t feed their families and ultimately, they’re going to do what they need in order to put food on the table.

The first question was what industry had a labor supply issue and therefore would hire people with criminal histories? That’s the first hurdle, just getting somebody into a job. Then the second thing that was important to us was to find an industry that pays a living wage. Because when people get out of prison, they’re not starting at ground zero. They’re starting six feet under. Their credit is completely shot. They are in debt. They don’t have access to bank accounts. They oftentimes don’t know how to invest their money into retirement plans. The financial foundations that build wealth and help their kids lead a life that is different from their parents are just not there.

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Trucking is an $875 billion dollar industry that employes 3.5 million truck drivers across the nation. In fact, truck driving is the most common job in 29 of 50 states. And because there is such a labor supply issue, many companies are willing to hire people with criminal histories. It’s also helpful that trucks have GPS systems and inventory management systems to allow the companies to track the truck at all times. We’re able to get drivers into local jobs so they are home every night. These are jobs with starting salaries up to $100,000 a year. It’s relatively cheap to get somebody trained in this field – about $7000 – and we can do it in 45 days. We built technology that allows us to deploy the solution anywhere across the nation. It’s scalable and we can use the tech platform to automate most of our program processes. Drivers don’t need the technology or social or office skills that other jobs do. So it’s an easier on ramp to help somebody get into a position where they could find success and break generational poverty and recidivism that usually plagues these families for decades. All these things in combination led to the realization that trucking is by far one of the best industries we could scale in.

What is FreeWorld’s business model? With whom do you partner?

Wang: We have three different revenue streams. One is our “pay it forward” program. That’s where we invest all the capital up front to help somebody get into their career. Once you are successful in your career making at least $45,000 to $50,000 per year depending on your tax bracket, then you pay 10% to help the next person go through school. If you don’t make that amount, then you don’t pay a thing. One reason is we think it’s important that our graduates have the ability to reinvest in the community that they live in. I look back to when I was arrested, and I realized that I hurt my community. Now that I’m in a better place in my life, I feel like is my duty and responsibility to pay back what is essentially an unpayable debt, which is the hurt and harm I caused my victims. And that is the same mindset that we want to instill in every single student who goes through our program. Regardless of the circumstance and environment, the fact that we committed a crime and went to prison means that we hurt somebody somewhere. Once you’re on your feet, we need you to pay it forward so that other people can avoid prison sentences and prevent other victims. The second revenue stream is state and local government programs that pay for our training and pay us as training providers. The third is trucking companies that pay us a fee for placing drivers at their companies, and because of the large labor supply issues, these fees can be quite lucrative. We’re at the early stages of testing the government and trucking fee models, but we have a lot of optimism that this can lead to us becoming a fully self-sustaining organization within the next three to five years.

What is FreeWorld’s impact?

Wang: The crazy thing about trucking and those who have been incarcerated is that

once you get into the industry and get a little bit of experience, you suddenly have recruiters who are blowing up your phone with job opportunities. And it’s a great feeling for somebody with a criminal history, because the status quo is that you apply to 100 jobs and 100 companies say no, but with our program suddenly you’re in a position where you have all the leverage, and you can pick and choose. I think that’s a lot of what contributes to such a low recidivism rate for us. Because outside of the ability for our drivers to be able to take care of their families for the first time in a long time, they suddenly feel valued in society. They suddenly don’t feel like a leper in society, and they feel like the work they’re doing has a purpose behind it that they can have pride in. Now they are a person who is responsible for keeping America running. It changes how you think about yourself and helps you get past some of the self-limiting beliefs you might have built up over years of the system telling you that you’ll never amount to anything, you’re good for nothing, you’re scum of the earth, that you committed a crime and therefore should pay for it the rest of your life.

We have a less than five percent recidivism rate compared to the national average of 72%. Ninety percent of our students get a job within three months of graduating. The starting wages are anywhere between $65,000 and $100,000 per year. And we have an 86% one-year retention rate in the trucking industry. The trucking industry without FreeWorld’s program has a 92% turnover rate, meaning that a company will essentially hire two people to get one person to stay by the end of the year. So we’re pretty proud of the metrics we’ve been able to deliver. But most importantly, for the first-time fathers and mothers finally have the money to put a Christmas present under the tree and be a role model for their kids. And that’s how we really think about our impact. It’s one part intervention, helping the parents get into a better situation, but the second part is prevention, making sure the next generation of kids doesn’t follow in their parents’ initial footsteps.

What’s next for FreeWorld?

Wang: We’re known for our trucking program, but we probably don’t talk about technology enough. Part of what makes us successful is we’re trying to create an environment where reentry is as easy as pushing a button. What that means in practice for us today is that when somebody gets out and they don’t have a birth certificate or Social Security card, they can push a button and we get those documents for them. They click a button and get a text message from Uber to schedule a ride to the appointment at the DMV. We pay for it all. In the future, we’re going to get into dignified housing at scale, childcare, and banking. We’re already building out a credit score tool that automatically fixes people’s credit score on their behalf.

We have amazing funders like Eric Schmidt, the CEO of Google, Stand Together, and Quality Jobs Fund. We’ve got big backers funding our work, but it’s a big problem. There are people who come to our program desperate for this opportunity, but we are resource-constrained. Most importantly for this upcoming year, we’re focused on building critical mass in the cities we focus on, so we can turn on the engines for revenue and serve more people.

We’re a young organization. I think we’ve had quite a bit of success, but it’s not like we’re serving 100,000 people per year. And when you look at the scope of the problem, one in three American adults has a criminal history. That’s about 70 million people. To put that into perspective, the same number of people in the U.S. have college degrees. The tools and systems we’ve built can become a poverty alleviation tool that can be scaled globally. But until we get to a point that we have an engine running that is impacting millions of lives, the last thing we as a young startup should do is lose focus. So we’re staying dead focused on our target, which right now is only for people with criminal records.

The U.S. has one of the highest incarceration rates in the world, with almost 1.7 million Americans in prison. What do you wish others knew about those with a criminal background, and what advice do you have for those trying to reinvent themselves?

Wang: The first thing is building empathy, and the way I’ve done that is by asking people, “what would you do if you were only known for the worst thing you’ve ever done? What would that look like? Would you be called liar, cheater, thief?” If we’re honest with ourselves, I think most people can honestly say that they have done something where they could have been arrested, but they weren’t. And because of that they had a very different trajectory in life.

That’s not so for the people who come from my background, from my neighborhoods, who go to prison. They’re oftentimes coming out of horrific situations and neighborhoods filled with gang violence and drugs, where there are very few options. And sometimes you make a decision in the spur of the moment or because of the situation or environment that you otherwise would not have if you had the space or the safety to be able to think things through. So, what would you do if you were only known for the worst thing you’ve ever done?

The second thing is, what kind of neighbor do we want to have once these people get released? Because 95% of people who go to prison will end up getting released at some point. Incarceration has skyrocketed under the status quo. Seventy-six percent of people who go to prison will go back to prison within five years. This is a horrible solution to public safety. And by the way, we’re spending $182 billion on an industry that is failing us. So just imagine what a significant reduction in recidivism could mean if we reinvested this money that is currently being spent on human suffering and use that money instead to educate the next generation of kids or build infrastructure.

The conversation has been edited and condensed for clarity. Check out my other columns here.